A 1970s graphic designer is thrown into psychological turmoil when his girlfriend breaks up with him.

Upon discovering compromising pictures of Charles Swan III (Charlie Sheen) with other women, a distraught Ivana (Katheryn Winnick) leaves with the slam of a door. In an effort to throw away the collection of shoes left behind by his ex-girlfriend, the hapless and stressed out Charles ends up with his car in the swimming pool of a record producer.

Taken to a hospital for examination, Charles is visited by his sister Izzy (Patricia Arquette) and her two sons, his best friend Kirby Star (Jason Schwartzman), and his business manager Saul (Bill Murray). As he waits for the doctor (Dermot Mulroney) to arrive with the test results, Charles flashes between his happy memories with Ivana, and fantasies such as him rising from a coffin like Dracula to dance with his widow dressed ex-girlfriends and another which has him and his buddy Kirby as cowboys being chased by a band of beautiful Native Indians led by Ivana to a cave. Driven to distraction Charlie plants a microphone to discover whether or not Ivana has left him for another man; however, the more critical question that needs to be answered is whether or not he can move on with his life.

The opening which dissects the brain of the title character features a cut out animation sequence that would fit in nicely with the psychedelic sensibilities of The Beatles’ classic Yellow Submarine (1968). The surreal nature of the settings and satirical humour harkens to something that Wes Anderson would have done which is not surprising as the two filmmakers co-wrote The Darjeeling Limited (2007) and Moonrise Kingdom (2012) together. Katheryn Winnick (Love and Other Drugs) does an uninspiring portrayal of the elusive love interest while Bill Murray (Hyde Park on Hudson) and Jason Schwartzman (Scott Pilgrim vs. the World) are reliable sidekicks with deadpan wit. It is shame that Mary Elizabeth Winstead (A Good Day to Die Hard) only has a small part as I sense that the movie would have been better if she had been give more of a role to play. As for Charlie Sheen (Wall Street) all the media coverage dealing with him having a mental meltdown makes the part of the self-absorbed womaniser midst an existential crisis feel like old news.